ASCIDIDEMIN

ID: ALA340160

Max Phase: Preclinical

Molecular Formula: C18H9N3O

Molecular Weight: 283.29

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (1): Ascididemin
Synonyms from Alternative Forms(1):

    Canonical SMILES:  O=C1c2cccnc2-c2nccc3c2c1nc1ccccc13

    Standard InChI:  InChI=1S/C18H9N3O/c22-18-12-5-3-8-19-15(12)16-14-11(7-9-20-16)10-4-1-2-6-13(10)21-17(14)18/h1-9H

    Standard InChI Key:  BTAIBIXHXSXUFN-UHFFFAOYSA-N

    Associated Targets(Human)

    HCT-116 91556 Activities

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    MCF7 126967 Activities

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    U-87 MG 3946 Activities

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    U373 MG 658 Activities

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    T-24 2342 Activities

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    J82 505 Activities

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    HCT-15 51914 Activities

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    LoVo 4724 Activities

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    T47D 39041 Activities

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    A549 127892 Activities

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    A-427 643 Activities

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    PC-3 62116 Activities

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    SN12C 47755 Activities

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    MDA-N 28205 Activities

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    NCI-H23 49055 Activities

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    UO-31 46270 Activities

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    ACHN 49357 Activities

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    HL-60 67320 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HOP-92 41141 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    DU-145 51482 Activities

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    SF-539 44845 Activities

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    SK-MEL-5 47095 Activities

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    Malme-3M 44254 Activities

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    A498 42825 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    K562 73714 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    OVCAR-3 48710 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    MOLT-4 49676 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HOP-62 47048 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    U-251 51189 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    NCI/ADR-RES 33767 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    OVCAR-5 45555 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    OVCAR-8 47708 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SNB-19 46794 Activities

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    SR 39847 Activities

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    MDA-MB-231 73002 Activities

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    SW-620 52400 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    TK-10 45540 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    NCI-H522 44358 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    KM12 47707 Activities

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    M14 47487 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    RPMI-8226 44974 Activities

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    NCI-H322M 45589 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    OVCAR-4 44535 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    LOX IMVI 44321 Activities

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    BT-549 31254 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SK-MEL-2 46422 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SNB-75 44215 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SF-268 49410 Activities

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    EKVX 44102 Activities

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    SK-OV-3 52876 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    NCI-H460 60772 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    UACC-62 47335 Activities

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    MDA-MB-435 38290 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    CAKI-1 44928 Activities

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    IGROV-1 47897 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SF-295 48000 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Hs-578T 29457 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    UACC-257 46019 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    786-0 47912 Activities

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    CCRF-CEM 65223 Activities

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    NCI-H226 44470 Activities

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    SK-MEL-28 48833 Activities

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    HT-29 80576 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    RXF 393 41971 Activities

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    COLO 205 50209 Activities

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    DNA topoisomerase II alpha 6317 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    A-375 9258 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SW480 6023 Activities

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    Telomerase reverse transcriptase 2428 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    P388 20296 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    CHO 4503 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    BSC-1 357 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Bacillus subtilis 32866 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Escherichia coli 133304 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Pseudomonas aeruginosa 123386 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Candida albicans 78123 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trichophyton benhamiae 1686 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Amorphotheca resinae 75 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mycobacterium tuberculosis 203094 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Vero 26788 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Micrococcus luteus 7463 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trypanosoma brucei brucei 13300 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mycolicibacterium aurum 354 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: YesOral: NoChemical Probe: NoParenteral: No
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: NoAvailability: NoProdrug: No

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 283.29Molecular Weight (Monoisotopic): 283.0746AlogP: 3.39#Rotatable Bonds: 0
    Polar Surface Area: 55.74Molecular Species: NEUTRALHBA: 4HBD: 0
    #RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
    CX Acidic pKa: CX Basic pKa: 1.89CX LogP: 2.98CX LogD: 2.98
    Aromatic Rings: 4Heavy Atoms: 22QED Weighted: 0.41Np Likeness Score: 0.46

    References

    1. Delfourne E, Darro F, Portefaix P, Galaup C, Bayssade S, Bouteillé A, Le Corre L, Bastide J, Collignon F, Lesur B, Frydman A, Kiss R..  (2002)  Synthesis and in vitro antitumor activity of novel ring D analogues of the marine pyridoacridine ascididemin: structure-activity relationship.,  45  (17): [PMID:12166949] [10.1021/jm0208774]
    2. Lindsay BS, Barrows LR, Copp BR.  (1995)  Structural requirements for biological activity of the marine alkaloid ascididemin,  (7): [10.1016/0960-894X(95)00106-4]
    3. Copp BR, Christiansen HC, Lindsay BS, G Franzblau S..  (2005)  Identification of heteroarylenamines as a new class of antituberculosis lead molecules.,  15  (18): [PMID:16005211] [10.1016/j.bmcl.2005.06.010]
    4. Bontemps N, Bry D, López-Legentil S, Simon-Levert A, Long C, Banaigs B..  (2010)  Structures and antimicrobial activities of pyridoacridine alkaloids isolated from different chromotypes of the ascidian Cystodytes dellechiajei.,  73  (6): [PMID:20491501] [10.1021/np900751k]
    5. Camp D, Davis RA, Campitelli M, Ebdon J, Quinn RJ..  (2012)  Drug-like properties: guiding principles for the design of natural product libraries.,  75  (1): [PMID:22204643] [10.1021/np200687v]
    6. PubChem BioAssay data set, 
    7. García A, Bocanegra-García V, Palma-Nicolás JP, Rivera G..  (2012)  Recent advances in antitubercular natural products.,  49  [PMID:22280816] [10.1016/j.ejmech.2011.12.029]
    8. Kumar A, Kumar S, Jain S, Kumar P, Goyal R.  (2013)  Study of binding of pyridoacridine alkaloids on topoisomerase II using in silico tools,  22  (11): [10.1007/s00044-013-0496-5]
    9. Bontemps N, Gattacceca F, Long C, Thomas OP, Banaigs B..  (2013)  Additional cytotoxic pyridoacridine alkaloids from the ascidian Cystodytes violatinctus and biogenetic considerations.,  76  (9): [PMID:23961991] [10.1021/np400284z]
    10. Claes P, Cappoen D, Mbala BM, Jacobs J, Mertens B, Mathys V, Verschaeve L, Huygen K, De Kimpe N..  (2013)  Synthesis and antimycobacterial activity of analogues of the bioactive natural products sampangine and cleistopholine.,  67  [PMID:23850570] [10.1016/j.ejmech.2013.06.010]
    11. Chen JL, Sperry J, Ip NY, Brimble MA.  (2011)  Natural products targeting telomere maintenance,  (4): [10.1039/C0MD00241K]
    12. Swain SS, Pati S, Hussain T..  (2022)  Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation.,  232  [PMID:35168150] [10.1016/j.ejmech.2022.114173]
    13. Mishra SK, Tripathi G, Kishore N, Singh RK, Singh A, Tiwari VK..  (2017)  Drug development against tuberculosis: Impact of alkaloids.,  137  [PMID:28628823] [10.1016/j.ejmech.2017.06.005]